Feels like the first time
by BJ30
Summary: With their birthday fast approaching, the chipmunks finalize their wish list. All Simon wants is something his brothers have already done: lose their virginity. Will smooth moves and fancy talk be enough for Jeanette, or will Simon be rejected again?
1. The tease

With their birthday fast approaching, the chipmunks were finalizing their wish list.

"So, what do you want, Theo?"

"I want to spend a nice night alone with Eleanor. Maybe go outside and watch the sunset. You know how she loves that. What about you, Alvin?"

"A cool make out session with Britt followed by an incredible night of… well, you know…"

Simon sat alone in the corner, sulking.

"Si? What's wrong?"

"I never get what I want for my birthday…"

"What are you talking about? Theo and I spent the entire day with you."

"Yeah, three years ago! I mean something else, Alvin. You and Britt have done it. Theo and Eleanor have done it. Why can't Jeanette and I? All I want for my birthday is to lose my virginity to her, and yet she keeps teasing me night after night! What more do I have to do?"

Alvin hugged his brother, patting him on the back.

"Tell you what. How about Theo and I set the mood and you take care of the rest?"

"I don't know…"

"Come on, Si. Oh! We'll have to make you look extra sexy for her too."

"Maybe she's shy about doing it for the first time…oh well."

"Simon Seville, listen to me. You are going to put the moves on that fine piece of tail and that's final!" Alvin pointed at Simon angrily.

"Okay! Our birthday isn't until tomorrow, though. What do we do until then?"

"How about a warm-up, huh? You and I? Come on… give me some sugar, Si."

"No, Alvin. I want tomorrow night to me magical for her and I. Why, we've only kissed one time, and that was an accident. We've never kissed out of pure love."

"Si, how is kissing an accident?"

"Well, we were walking backstage after a concert when she tripped over a cable and I caught her. Our lips touched for a split second before she stood back up and kept on walking. Let me tell you, though. That split second was heaven!"

"I bet, Simon. But that doesn't count as a kiss. It was an accident. Wait until tomorrow night when it really means something."

Simon left his brother's side and went to Jeanette's bed, where she was reading. Alvin decided to hide under his covers and secretly watch his brother. Jeanette hugged Simon as he sat down next to her, and then resumed reading.

"What are you reading, Jeanette?"

"A very cute story about wild animals. Did you know that wild chipmunks produce a litter…"

"… of four to five babies at once?"

"Yeah! And that they are on their own…

"…at about eight weeks old?

"Wow, you really are smart, Simon."

"Thanks, Jeanette, so are you."

Alvin had a smile grow across his face as he saw the two slowly slide close together. As Simon puckered his lips and prepared for a kiss, Jeanette turned back to her book. Disappointed, Simon stood up and returned to Alvin.

"See what I mean? She's a cock tease! She loves to mess with me, Alvin. I don't know how much more I can take of it. Do you think Brittney would do it with me?"

"Wha.. what? My girl? Do it with you? I know you're desperate for action but you can't do it with her. She's my girl. Just work on Jeanette tomorrow. With what Theo and I got planned, she'll find you irresistible!"

"I hope so, Alvin. I really hope so."


	2. Getting close

**Chapter Two**

Dave woke everyone early the following morning by singing happy birthday.

"No offense Dave, but you don't sing that good."

"I know, Simon. Now come on! It's your birthday. I have gifts for you."

The chipmunks rushed out of their bedroom where three presents waited them.

"Uh, Dave? Where are Simon and Theodore's presents?" Alvin laughed.

"Relax, Alvin. You get the red box, Simon gets the blue and Theodore gets the green."

Theodore held onto Eleanor's hand and walked over to his gift.

"Would you like to help me open it, Eleanor?"

Together, they tore into the shiny paper revealing a small box. Theo opened the box and gasped.

"Is it… it is! Seasons one through four of Meerkat Manor! Thanks Dave! Come on, Eleanor. Let's go watch it!"

The duo ran toward the tv while Alvin was just opening his gift. He stared at Dave and then back at Brittney.

"Oh yeah! The best racing game to ever hit the gaming world. You are awesome, Dave. Come on, Britt. Betcha I can beat you to the finish line!"

"Oh… It is SO on, Alvin. We can use the tv in our room. Come on!"

Simon hung his head low, staring at the floor.

"Simon, is something wrong? Why are you not opening your gift?"

"I don't know. I just don't get too excited about birthdays, it seems. Sorry, Dave."

"That's okay. At least open your present."

Simon began unwrapping his gift while Jeanette watched. Simon was amazed to find not only a new pair of glasses, but two complete outfits and a new computer dictionary, encyclopedia and thesaurus.

"Dave, you know me too well. It is perfect!"

"Go on, and try those new glasses on. I wanna see how you look in them." Commented Jeanette.

Simon removed his old glasses and placed his new ones on.

"Wow… I can see twice as good now. Jeanette. Do you always look that… hot?"

"Simon!"

"What? She does, Dave. Now let's get that new shirt on."

Simon removed his shirt and slipped one of the new ones on. Jeanette commented him, while Simon was busy taking care of his new things. Simon went over to the computer and took a look at his new gifts.

"This is amazing. I'm going to learn so much with this!" Simon said, clicking through pages of text on the screen.

Jeanette sighed contently as she rested her head on Simon's shoulder and stared at the computer scree.

"So, how do you like your gifts? I helped Dave pick out the glasses."

"You did a good job, Jeanette. I love you."

"Aww…. I love you too, Simon."

Simon leaned closer to Jeanette as she continued staring at the screen. Simon stared at Jeanette and puckered his lips. Not noticing Simon, Jeanette jumped from the chair and ran from the room.

"Damn it! I was so close!" Simon shouted.

He jumped from the chair and headed toward where Alvin and Brittney were still playing games. He sulked on the corner of his bed, getting Brittney's attention. She walked over to Simon, who was on the edge of crying.

"Simon? What's wrong?"

"Jeanette. She's ignoring me."

"Oh Simon. She's not ignoring you. She loves you so much."

"She should at least let me kiss her, then. I mean, come on! It's harmless."

"I know, Simon. Maybe that's why she's in the bathroom right now putting on her new outfit…oops. That was supposed to be a surprise."

"New outfit? What's it look like?"

Brittney placed her hand over her mouth and joined Alvin again. Simon sat up and started to picture what Jeanette's new outfit looked like and what it might mean for them.

Simon heard a knock at the door as Jeanette entered the room. Simon's eyes grew in surprise as Jeanette walked in. She was wearing a blue sequin dress along with shoes that shined as well. Her hair was combed and straight, with her tail nice and bouncy.

"Uhhh…. Do I know you?"

"It's me, silly."

Alvin elbowed Brittney and pointed to the door. Together they ran for the door and closed it.

"Sorry for running away earlier. It was wrong."

"No, it was worth it. You look great. Now come over here and sit next to me, would you?"

Jeanette nodded and took a seat on Simon's bed. Jeanette grabbed hold of Simon's hand and again rested her head onto his shoulder. Jeanette reached around and placed her hand on Simon's back. Simon didn't react. He had been here before: getting ready for a kiss yet being denied so many times. As Jeanette removed her glasses so did Simon. 'this is new' he thought. She smiled and winked, and puckered her lips.

'This is it… don't mess it up, Simon.' He thought as he leaned in, and locked lips with Jeanette….


	3. At long last

**Chapter Three**

The second his lips touched Jeanette's, Simon thought 'wow… this is incredible!' He closed his eyes and placed his hand around Jeanette, pulling her close. She moved her tongue around, causing Simon to squeal in delight. She gently brushed his hair back a few times before pulling herself away and breaking the kiss.

"That was great, Simon. Simon? Are… are you okay?"

Simon was sitting completely still, staring at her.

"That was the most amazing thing ever! That's better than every concert we've been in combined! I hate to ask, but could you do that again?"

"Of course."

Simon leaned in and the duo planted their lips together again. This time however, Simon could hear soft music playing in the background.

"I swear, I had NOTHING to do with that, Jeanette."

"That's okay, Simon. I did."

"You?"

"Of course. I heard from the girls that you have to set the right mood, don't you?"

"I don't know! I've never done anything like this before."

"Neither have I. Just let instinct take over, Simon."

As she kissed his cheek, Simon blushed. 'I've been wanting this forever.' Simon thought. 'I hope I don't disappoint her.'

The duo continued making out as Jeanette gently pushed Simon onto his back. She then removed his shirt, along with hers. He wanted to say something, but was enjoying himself too much to object. Simon reached down and removed his pants.

"Oh… so that's what they look like…" commented Jeanette as she removed her pants as well, tossing them aside.

Simon shivered as he felt warm flesh completely surround his penis. He looked up and saw Jeanette leaning forward for a kiss. He obliged, and kissed her just as she started going at it. She could barely get started before Simon yelped in excitement.

"Oh… oh my… don't stop, Jeanette. That is incredible!"

Jeanette winked at him as she started going even faster. Simon then felt a strange feeling coming from between his legs. He could feel the pressure start to build as Jeanette continued.

"Oh Simon! You are… ooooohhh…" Jeanette screeched as Simon could no longer contain himself, letting loose a wave of seed into her body. She dismounted Simon a few seconds later and rubbed her hand around his shaft. She then started licking her hand clean.

"Funny… that doesn't taste as sweet as ice cream. It's kinda salty."

Simon pulled Jeanette close to him and kissed her wildly.

"Simon! What got into you all of the sudden?"

"You just gave me something I've been waiting eons for. I finally got to lose my virginity to a beautiful girl like you. It was so worth the wait!"

"I had fun too. I think that's how you do it…."

"Either way, I'm not complaining Jeanette. You are one very special lady. I love you!"

"Aww… I love you too. Come on. Let's get dressed and get back out there."

"All right."

Simon gathered his clothes and waited for Jeanette to finish putting on her dress. As the duo opened the bedroom door, Simon saw his brothers and the girls waiting for them.

"So, did you two… you know. Do it?" asked Brittney.

Simon blushed and stared at Jeanette.

"They did! He finally did it. Way to go, Si!" Theodore cheered.

"Thanks… I think."

"Hey Brittney, you lied."

"How?"

Jeanette pulled her sister in close and whispered 'It does NOT taste like ice cream.'

Brittney giggled and apologized to her.

"This has been the greatest birthday ever, you guys. Just one question, though. Who was responsible for that music? Oh! And her dress as well."

"Well, her dress was Eleanor's idea, while your brothers were responsible for that music. Was it good?"

"It was great! I have the best girl ever!" Simon shouted, causing Jeanette to blush. Simon smiled as he pulled her in close and gave her a kiss.

"Ooo... he's better at it than you, Alvin." Brittney said, causing the group to laugh. "Just kidding, Alvin. Come on. I think you and I have some exploring of our own to do. So do Theo and Ele."

Alvin led Brittney into the bedroom while Theodore and Eleanor walked outside. Jeanette latched onto Simon's hand and walked out to the couch to start watching tv.

"Simon, sorry about taking so long. Your brothers were the ones that convinced me to do it."

"You mean Alvin and Theo? Why would they do that?"

"They care about you, Si. They want to see you happy and based on what I saw in the bedroom, you can't get much happier than that."

"I don't think it's possible."

"Well, I hope that our friendship can do nothing but get stronger from here." Jeanette puckered up again and gave Simon a kiss on the cheek.

"I have a great feeling it will."


End file.
